Brønsted base-catalyzed α-oxygenation of carbonyl compounds utilizing the [1,2]-phospha-Brook rearrangement
Literature Information
Publication Date
2015-04-29
DOI
10.1039/C5QO00108K
Impact Factor
5.281
Authors
Azusa Kondoh
View Original
Abstract
A novel α-oxygenation reaction of carbonyl compounds was developed by utilizing the [1,2]-phospha-Brook rearrangement under Brønsted base catalysis. The reaction proceeds via the oxidation of enolates followed by the [1,2]-phospha-Brook rearrangement to afford α-oxygenated ester derivatives from easily accessible substrates having high functional group tolerance. In addition, the atom-economical tandem reaction of α-diethylphosphono ester derivatives with oxaziridines, which involves a carbon–carbon forming process in addition to α-oxygenation, was established under the low temperature conditions.
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Source Journal
Organic Chemistry Frontiers
CiteScore:
7.8
Self-citation Rate:
8.7%
Articles per Year:
724
Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry
Recommended Compounds
(S)-(9H-Fluoren-9-yl)methyl (pyrrolidin-2-ylmethyl)carbamate hydrochloride
CAS Number:
1217813-15-4
Molecular Formula:
C20H23ClN2O2
![4-[(2-{2-[2-(2-Aminoethoxy)ethoxy]ethoxy}ethyl)amino]-2-(2,6-dioxo-3-piperidinyl)-1H-isoindole-1,3(2H)-dione structure](https://static.chemtradehub.com/structs/209/2093416-31-8-3162.webp "4-[(2-{2-[2-(2-Aminoethoxy)ethoxy]ethoxy}ethyl)amino]-2-(2,6-dioxo-3-piperidinyl)-1H-isoindole-1,3(2H)-dione structure")
4-[(2-{2-[2-(2-Aminoethoxy)ethoxy]ethoxy}ethyl)amino]-2-(2,6-dioxo-3-piperidinyl)-1H-isoindole-1,3(2H)-dione
CAS Number:
2093416-31-8
Molecular Formula:
C21H28N4O7
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